For the last 3 months I have been very focused on sales of our Interaction Engine system and we are doing well on that score. As a result, though, I have not really shaped the business plan and the structure of our company for the inevitable VC round to come. Getting funding has not been an urgent requirement and it seemed far better to generate real revenue and then go for funding.

So as we are chugging along, our work has gotten the attention of two VCs who reached out for a meeting. This was my first introduction to the world of VCs and I confess, the meetings were startling and sobering; leaving me strangely ambivalent about the journey ahead on this front.

VC meeting number 1.

It was a rainy, NY winter day and we decided to meet at a coffee shop. I knew that this fund was more an incubator type which offered me the potential of being part of a startup community. It seemed like a good idea that I perhaps become part of the NY “Tech/ CEO club” since now, I am an outlier. I don’t hang out in Meetup sessions and I am not trekking across the country chasing the cool tech conferences (OK – I confess I am going to SXSW but only because they asked me to speak).

I enter the coffee shop with only the vaguest sense of what the VC looked like (his Twitter pix was decidedly not very useful). It took me a solid 8 minutes to spot him. As I approach I see this 30ish guy with a quirky winter cone hat that was just 2 degrees “off” – IMO wandering into “silly land.” It was hard not to laugh out loud at the effect – but I held my composure.

I sit down and we start chatting. I was curious to understand his investing philosophy. His focus decidedly was on individual technologies – why Foursquare will be huge or how this new app model will revolutionize some trend or other. When I wondered with him about the lack of a clear business model which limits their practical use for marketers, he dismissed that concern with a wave of the hand. “Well, that’s won’t be a problem for long – once the old guard is gone.”

Wow. Clearly that meant me. I took his comment to mean that only the “newer” generation have the depth to understand new marketing technologies. I was dumbfounded and I was shaken. The gap between us was, technologically speaking, generational – perhaps never to be bridged. But mostly I was stunned at how immature his thinking was about how the business of marketing really works. I was shaken knowing his company was helping drive the evolution of marketing without a clue about what marketers really need.

The rest of the conversation was a haze TBH. I left traumatized and angry at how dismissive he was of the impracticality of his vision of marketing technology evolution.

VC meeting number 2

This CEO leads a well-respected large VC shop that does $2- 5MM deals. I had been introduced to this VC through a mutual colleague and we met at his office one snowy day. He sat down in comfortable business casual attire that was in keeping with his experienced CEO role.

We started by talking about his company which was relocating to the East Coast from the West Coast. Interesting move and I asked him why. “Increasingly the smart money is coming to NY as this where many of the major new media and marketing operating business trends are evolving,” he said.

This was my dream VC – he understood the space and the problem my company was trying to solve – how to practically create the “many to many” marketing model. We compared notes on how the technology in this space was similar to CRM in the 1990s – full of possibility but lacking in coordinated systems to activate the technology. I suggested that we are a bit like what Siebel who, at the time, integrated all the telemarketing technologies into the system we now know as CRM. I feel that is what we are doing for the emerging “many to many” marketing model. We met for a solid 90 minutes at which point he asked me “What next?” Shockingly, I had no “ask.” I had been so traumatized by the first VC, that I had not really expected a question like that. I stumbled around and just admitted – “I don’t know.”

But then I turned it around and asked him: “How would you categorize my company? We are part system integrator, part content and media company. We are a “creative shop” in that we create customer interactions with technology. Are we a tech company, a services company?”

I could see he was sensitive to the dilemma of my question. Finally, he said, “I would put you in the digital media space.” I was shocked until he hastened to add: “You need to be defined somehow so people know to work with you and help you.” But in his gentle smile I could see his answer left him unsatisfied as well.

We parted agreeing to keeping up the dialogue. As I walked out of his office, I felt cautiously optimistic that the work we are doing is needed in the market.

One thing I learned from both meetings – the journey of starting a company will continue to be a journey of surprise. I never expected to have so dramatically divergent experiences as I tentatively start down the path of funding my company – even if I don’t know exactly what type of company I am creating.

All I know is that the “smart investment money is going towards the business operating companies” and that’s me. Cool – right?

(Author’s Note: Originally written Jan 5, 2010 – but even more true today.)

CES has descended upon the psyche of the tech world so that it dominates most reports and tweets and attention.

We all wait with bated breath for the declared best new product, most innovative game, most outrageous consumer electronic gadget. We are, in effect, like kids with our noses up against the window pane of the biggest toy store in the world.

I should say that the hyper cool nature of CES is a fairly recent phenomenon. Back when I worked at AT&T, CES was an annual ritual that, frankly, rather inconveniently put a crimp on holiday festivities since many of us had to go the Las Vegas a week before to setup. There went New Year’s plans *sigh*. Sure it was fun to see what ingenious gadget was coming into the market, but make no mistake about it; CES was a serious B2B trade show where manufacturers worked hard to woo retailers into carrying their stuff. While there was some consumer coverage, mostly it was confined to the B2B press.

Then, somewhere in the last 4 years, I think driven by the gaming industry, Google, Apple and social media, it took on the glamour of the Oscars for tech set. If a product was even mentioned in a “from CES” report, that was cause for celebration (“I am so honored even to be nominated” kind of thing). CES went from being a B2B event to the event that plays itself out directly to consumers. That shift, in effect, caused CES to become the biggest consumer trade event of all time – even if every consumer is attending by proxy via social media.

But there’s more to it than that because at the current level of consumer exposure to the show, CES has transcended the trade show segment and was elevated to become a premier consumer media buy, kinda like SuperBowl. Think about with me. A media buy in SuperBowl was a strategy companies used to catapult themselves – think GoDaddy. This media buy cost a few million bucks, but if played right – you were made. I think CES has taken on that same level of media potential if you account for all the primary, secondary and tertiary coverage that live streaming and social media provide. And instead of a few thirty second spots, you get three days to strut your stuff. Make no mistake about – doing CES right is a multi-million affair. But the pay-off could be huge. In fact, it would not shock me if I learned that CES exceeded SuperBowl in the number of impressions delivered.

That’s awe inspiring. Never before has a trade show had that kind of reach and coverage. It seems cosmically fitting that new technology, e.g. social media, would elevate the very essence of CES itself.

“Mama never told me there’d be weeks like this…”

It has been a while since my last entry and I am relieved to say it is mostly for good reasons. Over the last few months, this little venture has begun to take hold – to wit:

I have been on the speaking tour about The Interaction Engine capping it off with a spiel at ad:tech this month.

We have closed two new clients – one in the consumer electronics space and one in the mobile app space.

I am getting better at presenting our system in meetings – now I can kinda explain it in about 30 minutes. It still falls far short of the 2 minute elevator pitch – but hey – we are getting better.

A number of marketing and technology companies have contacted us to “partner” – not sure what that means though

We have done a few presentations to media buying agencies as they are challenged to “buy” social media. They are interested in working with us (again – no idea what that means)

Most important – revenue is beginning to accrue

Yet, despite the clear progress and momentum – I recognize the utter fragility of this venture. Of the dozen or so folks that are part of this company – most (but not all) are getting paid some compensation. No one is getting what they deserve – yet.

But my biggest challenge is that as we get more noticed, there are far more opportunities that need to be assessed and prioritized. Fundamentally, these opportunities run along three basic lines:

Technology Partnerships – there are 4 companies that we are talking to now in the marketing technology space. These companies are anxious to partner with someone like us because often these tech companies have no easy distribution channel. A cool recommendation engine is nice – but it’s hard selling a “stand-alone” technology to a big brand or agency. As a quasi “system integrator” of social media technologies – they see our Interaction Engine as solving this major channel issue for them. thsi is not a pr﻿

Funding Options – my initial plan was to sell the Engine we have now (does not require any development) to generate about $500K in revenue. While that plan is still in play – I realize that getting to that sales threshold might take longer than I can wait to begin the second phase of this company – to develop/ sell “self-serve” integrated social media programs to SMB via web hosts. I am encouraged by experienced colleagues who tell me I can go get funding now with what we have. TBH, I am still unclear whether any VC would consider this investable. My colleagues are so confident that this can get funded that they are willing to spend their own time over the next few months to work on this. On the one hand, that’s a funding gift that I would be crazy to reject. But on the other hand, it will still require my time for an exercise that I’m not convinced will have a successful outcome. Getting VC funding is a huge time hog – not matter who helps you. I keep wanting to put it off or get a traditional loan to ease the short term cash crunch. this is since this is not any way understand how to make this spaceing this work. it is frustating to say the least but this need

Media Alliances – Unlike most other marketing technology companies, I focused on the technology platform but I built it within a holistic system that includes an organized set of content assets from a diversity of publishers. To me, content is not king – but rather the juicy bait to start the engagement process which is why I had to collect relevant content assets. So while I spend a considerable amount of time building these alliances – there are many more people looking to partner with us because so many content producers and writers have been caught in the tumult of “freep” (free and/ or cheap) digital content distribution. In our system, these folks have a voice and a stake, so we solve a problem for them too. The problem is deciding who we can take on.

Most interestingly (and yes – it is a surprise), it seems that our Interaction Engine System (a coordinated, tech mashup of a monetizable “community of interest”) is an approach that can integrate disparate marketing activities into an operational program. In essence, instead of pitching an individual program to a client where I have to plug into their operations – we are being seen as our own ecosystem and other marketing programs and/ or technologies have to plug into us. I won’t say I planned it that way – but I am loving how this is playing out.

Now on to my biggest “what’s keeping me up list?” for this entry:

Knowing which contacts are worth pursuing on the tech front, on the funding front and on the editorial front. The response to my presentations has been great – but overwhelming actually.

Keeping the pressure up on the sales front – our issue now is too many great leads and not enough time to follow them all up.

Keeping the team motivated and monetized – always a struggle whether you are a new company or an old one

The next four weeks tend to be intense because marketing budgets are being finalized so we need to keep the pressure up – yet people’s mind are on the holidays. This requires an elegant and thoughtful approach to sales (I hope we are up to it).

Day after day, it seems the ride I am on gets more thrilling, more scary and more substantial. As the stakes keep going up, Mama never told me there would be weeks like this where too much is happening too fast. But I guess that beats the other option: too little happening too slow; by a mile.

“So dear Mama – I am grateful you taught me to appreciate a good ride when I see one which is exactly what I am doing – even though it feels like I caught a tiger by the tail.”

The roller coaster ride feels thrilling and yet …

Last week I had some ups and downs. I was happily surprised to be asked to speak at ad:Tech NY this November and I got my press credentials approved for the Clinton Global Initiative. The Social Media Technology Resource Guide is coming along and the team is working hard on creating the Sports Community of Interest for a few properties. On the sales front, we closed a small client that is doing interesting things with their mobile site. On the product front, our CTO – Louis Libin ideated for a way to provide an “overlay” to existing sites using a combination of social media technologies that we put together. It’s a great way to capture our “systems” approach to social media within a marketing environment. This is all good 🙂

On the down side – I have to cancel a Sept 28 Meetup event we scheduled to launch the Social Media Technology Resource Guide site. We are delayed by about two – three weeks :(. I developed this free guide as a directory of social media technologies since I could not find one anywhere (and my apologies if one exists – I could not find it). I am more bummed about this than I should be. After all, the delay was because we are pitching some really excellent clients. That is always good. But I am disappointed that I am delayed nonetheless.

At a more philosophical level, though, this set-back triggered one of my bigger challenges — managing the extreme highs and lows. Good things taste almost too wonderful – disproportionate to their “real” good news-ness. And inevitable bumps that occur feel more extreme than they should. I know not all CEOs suffer from this – they are more even-keeled. Some compartmentalize to keep things in check. I see why that might work – but it’s not me. Still groping around on that one.

But on the positive side, more than anything, this time of year is special to me. Yom Kippur is just over and with it comes a potential for a new start. It is a time for refocused purpose, re-organized thinking and re-energized gratitude for all the people that are helping/ rooting for me. It is incumbent on me to hang onto to the intense feeling of positive potential that characterizes this time of year for as long as possible. I hope to rise to the occasion but I credit myself with a fair amount of talent in that department.

Now – onto the “what keeps me up” list:

Creating a simple way to communicate what we do -this is a carry over from last week and it remains a top priority. Some good progress on one hand but nothing substantive yet.

We have quite a few follow up conversations coming up soon. This is good news but they want to see “under the hood” which leads me back to point #1.

I see an undercurrent of “downsizing” already going on in the social media space. Bigger companies are buying up smaller companies if they are in any way related to social media, especially on the technology side. On the one hand – these roll ups don’t worry me at the moment because they lack a cogent system for integrating the technologies (programmatically if not literally), but I worry that there will be too much consolidation too fast leaving just really big guys and then lots of tiny fish. Hmm.

Now, how am I doing against the milestone list I posted last week:

3 page executive summary of engageSimply with financial outlook – some progress but not as much as I would like.

1 signed client using the entire new Interaction Engine platform – new “sports” channel may be first one to launch or Trust Web – but tantalizingly just out of reach (a note of frustration intended here).

For 3 decades there were three chairs at the marketing table — agencies, brands and the media. All 3 parts technologically evolved in a symbiotic “one:many” model to grow the business. Agencies “produced once and ran many times”; brands (one) had a message to get out to many and each media property created its media content for many people.

But Internet was a fourth chair that came to the table. It started to dominate the other three chairs utterly disrupting the “one:many” efficient, profitable marketing model in favor of a “many:many” model brought on by social media and mobile technologies.

As technology continued to evolve much faster than the other chairs at the table, the result of this disequilibrium was first felt by the media which suffered a near fatal blow. Agencies, now are feeling the full brunt of this dynamic largely because the “complexity” of social media is taking more and more of the traditional ad budgets.

So while the business has gotten more complex, agencies are trapped in an old “one:many” business model and have no clear way to evolve. Clients do not pay often for agency’s’ technological learning curves (how many agency folks were at TechCrunch Disrupt for instance???). And agencies can not charge $10,000 for a bunch of twitter updates (if you want to sleep peacefully at night).

That’s why in this new scenario even agencies that want to embrace complexity — can not because the profitable “one:many” marketing business model does not support the “many:many” business model. Case in point. Digital media buying agencies are paid as a percentage of billings, but since there are few billings in social media — they do not create those types of programs for their clients. There is no incentive for a digital agency to develop a program with no/ low billings and high complexity – now is there?

So before agencies can embrace marketing complexity – we have to figure out how to make money at it. Talk about complex.

I admit a certain hyper sensitivity to all things security when it comes to Internet. I worked at CA and then Comodo – both heavy players in the online security world. I learned about the scary things that can happen if you go online alone. It is not a pretty picture.

So it’s no wonder that I tend to have a zero tolerance to bad online security practices – among my friends, my family, my peers. I have even less tolerance (is that possible?) for online security industry practices that can allow 1,000 PCs to get infected before an ad is checked for malware.

That’s right! I recently learned that all the ad serving platforms check ads in their networks after it has been served. In the case of Right Media I am told an ad is served 1,000 times before it is checked. If the ad is malware – oh well – 1,000 PCs are likely to get infected. I was shocked TBH. And I was even more shocked to learn that according to all the large ad serving platforms it seemed perfectly OK (at least the 4 large ones) to check ads after they have been served already. I had the chance to press a rep from Right Media for an explanation about why are ads not checked before they are served. It was explained to me that the sheer tonnage of ads would make checking everything before it ran impractical.

That answer seemed pretty lame actually. And one does not have to look hard to see how this causes problem up and down the ad market value chain. Recently, TechCrunch and The Drudge Report were hit with malware on their sites served up by an ad in the network. http://news.cnet.com/8301-27080_3-20000353-245.html. The backlash was felt by the likes of Michael Arrington who had to explain the issue to his audience. I felt his pain, more keenly felt because I knew there was little he could do to make it better. It is likely to happen again – the only question is when.

Here we see most blatantly the bad things that happen when you detach consequences from accountability as is the case here. The ad server networks are the ones who serve up the ads, good or bad, but if there is fall-out, it is largely felt by the site that delivered the ad. That ruptures the basic laws of accountability and consequence which ultimately leaves at least 1,000 PCs infected with malware every time there is a virus outbreak.

Now I really do not understand the technological limits of checking ads within an ad networks – but how can it be OK to permit ads to be served before they are checked? Could it be that 1,000 is too small a number to worry about? And as the number of ads being served grows, will a higher 10,000 threshold be OK? Then maybe 100,000 will be a tolerable number?

Here is a challenge to the industry. Elinor Mills’ article on this subject mentions Bennie Smith, a vice president of exchange policy at Yahoo’s Right Media who I invite to respond here. Maybe I it got it wrong. Set the record straight – please – I really want to be wrong.

Better yet – I would love to start a dialogue to solve the problem – between agencies, ad networks, advertisers and the security industry. Sometimes talk is not enough. An alternative is needed – an alternating current. But more on that coming…